Anthracene derivative.



UNITED STAT t lts Pit? it N 'l till i HIE,

KARL THUN, OF ELBERFELD, GERMANY, ASSlGbIOlt TO FARBENFABRIKEN VORM. FRIEDR. BAYER & (10., OF ELBERFELD, GERMANY, A CORPORA- TION GERMANY.

ANTHRACENE DEREVATIVE.

Specification of Letters Patent.

Patented Feb. 19, 1907.

dppllcatiml filcd November 28, 1906. Serial No. 345,519.

Be it known that I, KARL THUN, a citizen of the German Empire, residing at Elbcr- 'feld, Kingdom of Prussia, Germany, have 5 invented new and useful imprm'emcnts in Anthracene Derivatives, of which the following is a specification.

have found that aminonryl-aminoan thra-quinons containing the amino group I in ortho position with regard to the arylamino group are converted into new compounds by treatment with aldehydes. The anthraquinon derivatives produced in this way, which are most probably azins, are crystalline and r practically insoluble in water. They can be converted by the action of sulfonalinpagents-for instance, by means of fuming sulfuric acidinto sulfonic acids, the salts of which are soluble in water and which dye Wool from acid-baths from blue to green shades of excellent fastness. The reaction takes place most probably, a. 9., in accordance with the following equation:

l l mi (Ill -Hi4) The dyestufl' deposits, while tatc, which can be purified by a crystalliza- I tion from glacial acetic acid, pyridin, &c. lt forms dark crystals practically insoluble in water. To transform this condensation product into the new dyestufl' sulfonic acid ten parts of the finely-1iulvcrizedcompound are dissolved in one hundred parts offuming sulfuric acid (three per cent of S();,.) The resulting mixture is then heated to from about ccntigra 'e until a test portion is clearly dissolved in hot water. After cooling, the mixture is stirred into Water and the sulfonic acid is separated by the additionof common salt iiltcrcd oil and dried. it is after being dried and pulverized a dark powder soluble in water with air ine color. It dycs wool fast blue shades.

Example ll. A mixture of ten parts of l-para.-tolylzamino-l-aiiiino-3-bromo-rmthraquinou (obtainable from para-toluidin and 1.? dibromo 2- amino anthraquinon) and one hundred parts of glacial acetic acid is heated on the watcrbath and ten parts of benzaldchyde are added to the 'IILlXtUIC. The reddishwiolct solution turns blue. The reaction is completed after from four to six hours heating. The newcondensationprodnot deposits while cooling in the shape of blue crystals practically insoluble in water. its sulfonic acid dyes wool blue.

The process is carried out in an analogous manner when starting from other orthoamino-arylamino-anthraquinons or from other aldchydcs.

Having now described my invention and in what manner the same is to be performed, what ll claim as new, and desire to secure by Letters Patent, is-

1. The herein-dcscribed new anthracene derivatives which can be obtained by treatin; amino-ar l amino -:u1tlnaquinons containing lhoainiuo group inortho position with regard to thc aryl-zunino group, with aldehydes, which new derivatives are crystalline and. whcu unsulfonated are practically insoluble in water, and which in the shape of their sullonic acids dye wool from blue to green shades, substantially as hereinbefore dcscrilwd.

2. The herein-dcscribed new anthracene derivative which can be obtained by treating l-p are tolyl amine 2 amino enthrequinon l In testimony whereof I have hereunto set with formaldehyde, which new derivative is my hand in the presence of tW01lbSOIibiIlg a dark crystalline powder which when unwitnesses. sulfoneted is practically insoluble in Water, KARL THUN. end which in the shape of'its sulfonic acid dyes wool blue shades, substantielly as here- I inbefore described.

Witnesses OTTO Keme, T. A. RITTERHAUS. 

